# US 10,117,878 B2 · Ligands for nematode nuclear receptors and uses thereof

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- Number: US 10,117,878 B2
- Document ID: US10117878B2
- Status: Granted
- Kind: B2
- Application number: 13/673,696
- Filed: 2012-11-09
- Published: 2013-05-30
- Granted: 2018-11-06
- Earliest claimed: 2006-03-08
- Assignees: Board of Regents, The University of Texas System
- Applicants: Board of Regents, University of Texas System
- Inventors: David J. Mangelsdorf; Richard J. Auchus; Daniel L. Motola; Carolyn L. Cummins; Kamalesh K. Sharma
- Web page: https://patentgrep.com/patent/US10117878B2

## CPC

- A61K 31/575: substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
- C07J 9/00: Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
- C07J 9/005: {containing a carboxylic function directly attached or attached by a chain containing only carbon atoms to the cyclopenta[a]hydrophenanthrene skeleton}
- Y02P 20/582: Recycling of unreacted starting or intermediate materials
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- C07J: STEROIDS (seco-steroids C07C)
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

An effective anti-nematode methodology entails contacting nematodes with a biologically effective amount of at least one compound according to formula I: where Q, Q′, R1, R2, and n are defined herein, or with a stereoisomer, solvate, or pharmaceutically acceptable salt of such compound.

## Claims

### Claim 1

A method for controlling the growth of a nematode, comprising contacting the nematode with a biologically effective amount of at least one compound according to formula I or a stereoisomer, or pharmaceutically acceptable salt thereof:
wherein each instance of independently is a single bond or a double bond; one of Q or Q′ is OH or SH and the other of Q or Q′ is hydrogen, or Q and Q′ together with the carbon atom to which they are attached form a carbonyl or thiocarbonyl group; R1 is selected from the group consisting of:
wherein each instance of independently is a single bond, or a double bond; and wherein R1 is optionally substituted with 1 to 2 substituents, each of which is independently selected from the group consisting of halo, (C1-C8)alkyl, NRR′, OR, and SR; R2 is a substituent on one or more carbon atoms in rings A, B, C, and D and, in each instance, is independently selected from the group consisting of halo, (C1-C8)alkyl, (C1-C8)haloalkyl, (C1-C8)hydroxyalkyl, NRR′, oxo, thione, OR, and SR; R and R′ are independently selected from the group consisting of hydrogen, (C1-C8)alkyl, (C1-C8)fluoroalkyl, and (C1-C8)hydroxyalkyl; and n is selected from the group consisting of 0, 1, or 2.

### Claim 2 (depends on 1)

The method according to claim 1, wherein the compound is selected from the group consisting of:

### Claim 3 (depends on 1)

The method according to claim 1, wherein the nematode is a parasitic nematode.

### Claim 4 (depends on 3)

The method according to claim 3, wherein the parasitic nematode is a member of an order selected from the group consisting of the Strongylida, Rhabditida, Ascaridida, Spirurida, Oxyurida, Enoplida, Tylenchida, and Dorylaimida nematode orders.

### Claim 5 (depends on 3)

The method according to claim 3, wherein the parasitic nematode is a member of a genus selected from the group consisting of Haemonchus, Oestertagia, Trichostrongylus, Cooperia, Dictyocaulus, Strongylus, Oesophagostomum, Syngamus, Nematodirus, Heligmosomoides, Nippostrongylus, Metastrongylus, Angiostrongylus, Acyclostoma, Necator, Uncinaria, Bunostomum, Strongyloides, Steinemema, Ascaris, Parascaris, Toxocara, Toxascaris, Baylisascaris, Anisakis, Pseudoterranova, Heterakis, Wuchereria, Brugia, Onchocerca, Dirofilaria, Loa, Thelazia, Dracunculus, Gnathostoma, Enterobius, Oxyuris, Syphacia, Trichinella, Trichuris, Capillaria, Globodera, Heterodera, Meloidogyne, Anguina, Ditylenchus, Hirschmanniella, Naccobus, Pratylenchus, Radopholus, Criconema, Tylenchulus, Paratylenchus, Aphelenchus, Bursaphelenchus, Longidorus, Xiphinema, Trichodorus, and Paratrichodorus nematode genera.

### Claim 6

A method of reducing nematode infestation of a plant that is infested or susceptible to infestation by a nematode population, comprising administering to the plant a biologically effective amount of at least one compound according to formula I or a stereoisomer, or pharmaceutically acceptable salt thereof:
wherein each instance of independently is a single bond or a double bond; one of Q or Q′ is OH or SH and the other of Q or Q′ is hydrogen, or Q and Q′ together with the carbon atom to which they are attached form a carbonyl or thiocarbonyl group; R1 is selected from the group consisting of:
wherein each instance of independently is a single bond, or a double bond and wherein R1 is optionally substituted with 1 to 2 substituents, each of which is independently selected from the group consisting of halo, (C1-C8)alkyl, (C1-C8)haloalkyl, (C1-C8)hydroxyalkyl, NRR′, OR, and SR; R2 is a substituent on one or more carbon atoms in rings A, B, C, and D and, in each instance, is independently selected from the group consisting of halo, (C1-C8)alkyl, (C1-C8)haloalkyl, (C1-C8)hydroxyalkyl, NRR′, oxo, thione, OR, and SR; R and R′ are independently selected from the group consisting of hydrogen, (C1-C8)alkyl, (C1-C8)fluoroalkyl, and (C1-C8)hydroxyalkyl; and n is selected from the group consisting of 0, 1, or 2.

### Claim 7 (depends on 6)

The method according to claim 6, wherein the administering comprises treating with the compound soil in which the plant is grown.

### Claim 8 (depends on 6)

The method according to claim 6, wherein the administering comprises treating with the compound a seed from which the plant is to be grown.

### Claim 9

A method of reducing a nematode infestation in a mammal, comprising administering to the mammal a therapeutically effective amount of at least one compound according to formula I or a stereoisomer, or pharmaceutically acceptable salt thereof:
wherein each instance of independently is a single bond or a double bond; one of Q or Q′ is OH or SH and the other of Q or Q′ is hydrogen, or Q and Q′ together with the carbon atom to which they are attached form a carbonyl or thiocarbonyl group; R1 is selected from the group consisting of:
wherein each instance of independently is a single bond, or a double bond and wherein R1 is optionally substituted with 1 to 2 substituents, each of which is independently selected from the group consisting of halo, (C1-C8)alkyl, (C1-C8)haloalkyl, (C1-C8)hydroxyalkyl, NRR′, OR, and SR; R2 is a substituent on one or more carbon atoms in rings A, B, C, and D and, in each instance, is independently selected from the group consisting of halo, (C1-C8)alkyl, (C1-C8)haloalkyl, (C1-C8)hydroxyalkyl, NRR′, oxo, thione, OR, and SR; R and R′ are independently selected from the group consisting of hydrogen, (C1-C8)alkyl, (C1-C8)fluoroalkyl, and (C1-C8)hydroxyalkyl; and n is selected from the group consisting of 0, 1, or 2.